CN113840872B - Phenol compound, resin composition, method for producing the same, and molded article - Google Patents
Phenol compound, resin composition, method for producing the same, and molded article Download PDFInfo
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- CN113840872B CN113840872B CN202080036904.3A CN202080036904A CN113840872B CN 113840872 B CN113840872 B CN 113840872B CN 202080036904 A CN202080036904 A CN 202080036904A CN 113840872 B CN113840872 B CN 113840872B
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- resin composition
- resin
- phenol compound
- styrene
- copolymers
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- -1 Phenol compound Chemical class 0.000 title claims abstract description 80
- 239000011342 resin composition Substances 0.000 title claims description 67
- 238000004519 manufacturing process Methods 0.000 title description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 229920005989 resin Polymers 0.000 claims description 46
- 239000011347 resin Substances 0.000 claims description 46
- 238000010438 heat treatment Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 21
- 238000000465 moulding Methods 0.000 claims description 16
- 150000002989 phenols Chemical class 0.000 claims description 10
- 229920001169 thermoplastic Polymers 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 57
- 229920000642 polymer Polymers 0.000 description 50
- 229920001577 copolymer Polymers 0.000 description 35
- 239000000243 solution Substances 0.000 description 24
- 238000000354 decomposition reaction Methods 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 20
- 229930185605 Bisphenol Natural products 0.000 description 18
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 18
- 239000004793 Polystyrene Substances 0.000 description 17
- 229920002223 polystyrene Polymers 0.000 description 17
- 239000000654 additive Substances 0.000 description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
- 239000005977 Ethylene Substances 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 229920002857 polybutadiene Polymers 0.000 description 10
- 239000005062 Polybutadiene Substances 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 9
- 150000001993 dienes Chemical class 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- 239000004743 Polypropylene Substances 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 229920001684 low density polyethylene Polymers 0.000 description 8
- 239000004702 low-density polyethylene Substances 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 239000004952 Polyamide Substances 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- 229920005992 thermoplastic resin Polymers 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- 239000004700 high-density polyethylene Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000004800 polyvinyl chloride Substances 0.000 description 5
- 229920000915 polyvinyl chloride Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 3
- SSADPHQCUURWSW-UHFFFAOYSA-N 3,9-bis(2,6-ditert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1OP1OCC2(COP(OC=3C(=CC(C)=CC=3C(C)(C)C)C(C)(C)C)OC2)CO1 SSADPHQCUURWSW-UHFFFAOYSA-N 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
- 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- IORUEKDKNHHQAL-UHFFFAOYSA-N [2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenyl] prop-2-enoate Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)OC(=O)C=C)=C1O IORUEKDKNHHQAL-UHFFFAOYSA-N 0.000 description 3
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 150000001925 cycloalkenes Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 229940116351 sebacate Drugs 0.000 description 3
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000013585 weight reducing agent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 2
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 description 2
- ILNDSSCEZZFNGE-UHFFFAOYSA-N 1,3-Di-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1 ILNDSSCEZZFNGE-UHFFFAOYSA-N 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- VTFXHGBOGGGYDO-UHFFFAOYSA-N 2,4-bis(dodecylsulfanylmethyl)-6-methylphenol Chemical compound CCCCCCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCCCCCC)=C1 VTFXHGBOGGGYDO-UHFFFAOYSA-N 0.000 description 2
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 2
- GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 description 2
- AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 description 2
- HCILJBJJZALOAL-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-n'-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]propanehydrazide Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 HCILJBJJZALOAL-UHFFFAOYSA-N 0.000 description 2
- QRLSTWVLSWCGBT-UHFFFAOYSA-N 4-((4,6-bis(octylthio)-1,3,5-triazin-2-yl)amino)-2,6-di-tert-butylphenol Chemical compound CCCCCCCCSC1=NC(SCCCCCCCC)=NC(NC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=N1 QRLSTWVLSWCGBT-UHFFFAOYSA-N 0.000 description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical group CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 2
- ZVVFVKJZNVSANF-UHFFFAOYSA-N 6-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]hexyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCCCCCCOC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 ZVVFVKJZNVSANF-UHFFFAOYSA-N 0.000 description 2
- OWXXKGVQBCBSFJ-UHFFFAOYSA-N 6-n-[3-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[2-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[3-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]ami Chemical compound N=1C(NCCCN(CCN(CCCNC=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)=NC(N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)=NC=1N(CCCC)C1CC(C)(C)N(C)C(C)(C)C1 OWXXKGVQBCBSFJ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229930182556 Polyacetal Natural products 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- STLLXWLDRUVCHL-UHFFFAOYSA-N [2-[1-[2-hydroxy-3,5-bis(2-methylbutan-2-yl)phenyl]ethyl]-4,6-bis(2-methylbutan-2-yl)phenyl] prop-2-enoate Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(C(C)C=2C(=C(C=C(C=2)C(C)(C)CC)C(C)(C)CC)OC(=O)C=C)=C1O STLLXWLDRUVCHL-UHFFFAOYSA-N 0.000 description 2
- 229920000800 acrylic rubber Polymers 0.000 description 2
- 229920002877 acrylic styrene acrylonitrile Polymers 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229940117927 ethylene oxide Drugs 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 229920000554 ionomer Polymers 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 229920000092 linear low density polyethylene Polymers 0.000 description 2
- 239000004707 linear low-density polyethylene Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
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- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000012994 photoredox catalyst Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001627 poly(4-methyl styrene) Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920003251 poly(α-methylstyrene) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000306 polymethylpentene Polymers 0.000 description 1
- 239000011116 polymethylpentene Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- XBFJAVXCNXDMBH-UHFFFAOYSA-N tetracyclo[6.2.1.1(3,6).0(2,7)]dodec-4-ene Chemical compound C1C(C23)C=CC1C3C1CC2CC1 XBFJAVXCNXDMBH-UHFFFAOYSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
Abstract
The present invention provides a phenol compound represented by the following general formula (I).
In the general formula (I), R1、R2Each independently represents a hydrogen atom or an alkyl group.
Description
Technical Field
The present invention relates to a phenol compound, a resin composition, a method for producing the same, and a molded article.
Background
In the production of the resin composition, a production process of heat-treating a polymer solution containing a polymerization solvent under reduced pressure and high temperature conditions is sometimes carried out. In this heat treatment, the polymer solution is usually treated at a temperature far higher than the boiling point of the polymerization solvent in order to remove the polymerization solvent, and thus the polymer obtained by the heat treatment may suffer from problems such as thermal deterioration and coloration. Therefore, an additive capable of reducing the problems such as thermal degradation due to heat treatment by adding to a resin composition has been developed.
For example, patent document 1 proposes a phenol compound which can prevent thermal degradation and coloration of a polymer when the polymer is subjected to a high-temperature treatment for separating the polymer from a polymer solution in the production of a butadiene-based polymer.
Prior art literature
Patent literature
Patent document 1: japanese patent laid-open No. 1-168643.
Disclosure of Invention
Problems to be solved by the invention
Here, when the resin (i.e., the polymer) is subjected to the heat treatment under the reduced pressure and high temperature conditions as described above in the production of the resin composition, the polymer may be decomposed, and thus the polymer may be thermally degraded.
Therefore, an additive is required which can sufficiently suppress decomposition of the resin even when heat treatment is performed under reduced pressure and high temperature conditions at the time of producing the resin composition. For this reason, it is required that not only the additive has the ability to inhibit the decomposition of the resin, but also the additive itself does not volatilize easily even when exposed to high temperature conditions.
However, the bisphenol monoacrylate compound described in patent document 1 and other known additives are insufficient in the ability to inhibit resin decomposition under reduced pressure and high temperature conditions, or are easily volatilized under high temperature conditions.
Accordingly, an object of the present invention is to provide a phenol compound which does not readily volatilize even when exposed to high temperature conditions and which is sufficiently high in the ability to inhibit resin decomposition under reduced pressure and high temperature conditions.
Further, the present invention aims to provide a resin composition comprising the above phenol compound and a method for producing the same.
Further, an object of the present invention is to provide a molded article formed from the above resin composition.
Solution for solving the problem
The present inventors have conducted intensive studies with a view to solving the above-mentioned problems. Then, the present inventors have newly found that a phenol compound satisfying a specific structure does not volatilize easily even when exposed to high temperature conditions, and is excellent in the ability to inhibit resin decomposition under reduced pressure and high temperature conditions, and completed the present invention.
That is, the present invention aims to advantageously solve the above-mentioned problems, and the phenol compound of the present invention is characterized by being represented by the following general formula (I).
[ chemical formula 1]
[ in the general formula (I), R1、R2Each independently represents a hydrogen atom or an alkyl group.]
Such phenol compounds having the above-specified structure do not volatilize easily even when exposed to high temperature conditions, and the ability to inhibit resin decomposition under reduced pressure and high temperature conditions is sufficiently high. Therefore, by adding the phenol compound to the resin composition, even when the resin composition is subjected to a treatment under reduced pressure or high temperature conditions, the decomposition of the resin can be sufficiently suppressed.
Among the phenol compounds of the present invention, R of the above general formula (I) is preferred1And R is2Each hydrogen atom. In other words, the phenol compound of the present invention is preferably a bisphenol monoacrylate compound. By blending the bisphenol monoacrylate compound in the resin composition, even when the resin composition is subjected to a treatment under reduced pressure and high temperature conditions, resin decomposition can be further sufficiently suppressed.
In the phenol compound of the present invention, R of the above general formula (I) is preferable1Is methyl and R2Is a hydrogen atom. In other words, the phenol compound of the present invention is preferably a bisphenol monomethacrylate compound. By blending the bisphenol monomethacrylate compound in the resin composition, even when the resin composition is treated by exposure to conditions of reduced pressure and high temperature, resin decomposition can be further sufficiently suppressed.
Further, the present invention aims to advantageously solve the above-mentioned problems, and the resin composition of the present invention is characterized by comprising a resin and any of the above-mentioned phenol compounds. If the resin composition contains at least any one of the phenol compounds as described above, resin decomposition can be sufficiently suppressed even in the case where the resin composition is subjected to a treatment under reduced pressure and high temperature conditions.
Here, the resin composition of the present invention is preferably a thermoplastic polymer. By blending a thermoplastic polymer as a resin and the above-described combination of phenol compounds in the resin composition, the ability to suppress resin decomposition under reduced pressure and high temperature conditions can be further effectively exerted.
The present invention is also directed to solving the above problems, and the molded article of the present invention is characterized by being obtained by molding the above resin composition. The molded article obtained by molding the resin composition has excellent properties.
Further, the present invention is to advantageously solve the above-mentioned problems, and the method for producing a resin composition of the present invention is characterized by comprising a heating step of heating a mixture comprising the above-mentioned resin and the above-mentioned phenol compound at 200 ℃ or higher under reduced pressure. By depressurizing and heating a mixture containing a resin and a predetermined phenol compound under predetermined conditions, a resin composition having good properties can be efficiently produced.
In the present specification, "under reduced pressure" means under an environment having an absolute pressure of 50kPa or less.
Effects of the invention
According to the present invention, it is possible to provide a phenol compound which does not volatilize easily even when exposed to high temperature conditions and which is sufficiently high in the ability to inhibit resin decomposition under reduced pressure and high temperature conditions.
Further, according to the present invention, a resin composition containing the above phenol compound and a method for efficiently producing the above resin composition can be provided.
Further, according to the present invention, a molded article obtained by molding the resin composition can be provided.
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail.
Here, the phenol compound of the present invention is preferably incorporated into a resin composition which can be treated under reduced pressure and high temperature conditions, particularly at the time of production and molding, since it does not volatilize easily even when exposed to high temperature conditions and the ability to inhibit resin decomposition under reduced pressure and high temperature conditions is sufficiently high. The resin composition of the present invention can be efficiently produced by the method for producing a resin composition of the present invention. Furthermore, the resin composition of the present invention can be preferably used as a material for the molded article of the present invention.
(phenol Compound)
The phenol compound of the present invention is a phenol compound represented by the following general formula (I).
[ chemical formula 2]
[ in the general formula (I), R1、R2Each independently represents a hydrogen atom or an alkyl group.]
The phenol compound of the present invention has a structure represented by the general formula (I), and therefore, does not volatilize easily even when exposed to high temperature conditions, and has a sufficiently high ability to inhibit decomposition of a resin under high temperature and reduced pressure conditions. Therefore, by adding the phenol compound to the resin composition, even when the resin composition is subjected to a treatment under reduced pressure and high temperature conditions, the decomposition of the resin can be sufficiently suppressed.
In the general formula (I), R1、R2The alkyl groups of (a) may be, for example, independently an alkyl group having 1 to 6 carbon atoms. The alkyl group having 1 to 6 carbon atoms is not particularly limited, and examples thereof include: alkyl groups having a linear, branched or cyclic structure such as methyl, ethyl, propyl, butyl, pentyl, hexyl and cyclohexyl groups.
Among them, R is preferable1、R2Each independently is a hydrogen atom or a methyl group.
More specifically, the phenol compound having a structure represented by the general formula (I) is preferably a phenol compound represented by any one of the following formulas (I-1) or (I-2).
[ chemical formula 3]
Further, the melting point of the phenol compound of the present invention is preferably 30℃or higher, more preferably 40℃or higher, preferably 200℃or lower, more preferably 150℃or lower, and still more preferably 100℃or lower. If the melting point of the phenol compound is not less than the above lower limit, the compound is solid at ordinary temperature, and therefore the handleability of the compound is excellent. If the melting point of the phenol compound is not higher than the upper limit, the resin is liable to fall below the drying temperature, the condensing temperature and the molding temperature of the resin, and the phenol compound is liable to be sufficiently melted when the molded article using the resin composition is produced, whereby the transparency of the obtained molded article can be improved.
The melting point of the phenol compound can be measured by the method described in examples.
(resin composition)
The resin composition of the present invention comprises a resin and the above phenol compound. The resin composition of the present invention contains the phenol compound described above, and therefore, even when the resin composition is subjected to a treatment under reduced pressure and high temperature conditions, resin decomposition can be sufficiently suppressed. The resin composition may optionally contain a solvent and an additive. The resin composition may be a solution obtained by dissolving a resin in a solvent at normal temperature and normal pressure (25 ℃ C., 1 atm), or may be a solid substance (for example, resin particles) containing a resin in a solid state.
The content of the predetermined phenol compound in the resin composition is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, still more preferably 10 parts by mass or less, and still more preferably 1.0 part by mass or less, when the content of the resin is 100 parts by mass.
< resin >
Here, as the resin contained in the resin composition of the present invention, all known polymers can be used depending on the application. Examples of such polymers include various polymers listed as component a in JP-A-3-207788.
Specific examples are as follows.
1. Polymers of mono-and diolefins, for example polypropylene, polyisobutene, polybutene, polymethylpentene, polyisoprene or polybutadiene; and polymers of cycloolefins, for example polymers of cyclopentene or norbornene, dicyclopentadiene, tetracyclododecene; polyethylene (which may or may not be crosslinked), such as High Density Polyethylene (HDPE), low Density Polyethylene (LDPE), and Linear Low Density Polyethylene (LLDPE).
2. Mixtures of the polymers described in 1 above, for example mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (e.g.PP/HDPE and PP/LDPE) and mixtures of different types of polyethylene (e.g.LDPE/HDPE). Copolymers of mono-and diolefins, and copolymers of either or both mono-and diolefins with either or both other vinyl monomers and cycloolefins, copolymers of cycloolefins, such as ethylene/propylene copolymers, linear Low Density Polyethylene (LLDPE) and Low Density Polyethylene (LDPE) and mixtures thereof, propylene/butene copolymers, ethylene/hexene copolymers, ethylene/methylpentene copolymers, ethylene/heptene copolymers, ethylene/octene copolymers, propylene/butadiene copolymers, isobutylene/isoprene copolymers, ethylene/alkyl acrylate copolymers, ethylene/alkyl methacrylate copolymers, ethylene/vinyl acetate or ethylene/acrylic acid copolymers and salts (ionomers) thereof; and terpolymers of ethylene with propylene and a diene such as hexadiene, dicyclopentadiene or ethylidene norbornene, ethylene/norbornene copolymers, ethylene/tetracyclododecene copolymers; and further mixtures of such copolymers with and with the polymers described in 1 above, for example polypropylene/ethylene-propylene copolymers, LDPE/EVA, LDPE/EAA, LLDPE/EVA and LLDPE/EAA.
3. Hydrocarbon resins (for example, having 5 to 9 carbon atoms).
4. Vinyl aromatic polymers such as polystyrene, poly (p-methylstyrene), poly (alpha-methylstyrene), polyvinylnaphthalene, polydiphenylethylene.
5. Copolymers of styrene or other vinyl aromatic with dienes or acrylic derivatives such as styrene/butadiene, styrene/isoprene, styrene/acrylonitrile, styrene/alkyl methacrylates, styrene/methyl styrene, styrene/vinyl naphthalene, styrene/methyl styrene/isoprene, styrene/vinyl naphthalene/isoprene, styrene/butadiene/alkyl acrylates, styrene/maleic anhydride, styrene/acrylonitrile/methyl acrylate; impact resistant blends made from styrene copolymers with other polymers such as polyacrylates, diene polymers or ethylene/propylene/diene terpolymers; and block copolymers of styrene, such as styrene/butadiene/styrene, styrene/isoprene/styrene, styrene/ethylene/butylene/styrene or styrene/ethylene/propylene/styrene.
6. Graft copolymers of styrene or alpha-methylstyrene, for example polybutadiene graft styrene, polybutadiene/styrene or polybutadiene/acrylonitrile graft styrene, polybutadiene graft styrene and acrylonitrile (or methacrylonitrile), polybutadiene graft styrene and maleic anhydride or maleimide, polybutadiene graft styrene, acrylonitrile and maleic anhydride or maleimide, polybutadiene graft acrylonitrile and methyl methacrylate, polybutadiene graft styrene and alkyl acrylate or alkyl methacrylate, ethylene/propylene/diene terpolymer graft styrene and acrylonitrile, polyalkylacrylate or polyalkylmethacrylate graft styrene and acrylonitrile, acrylate/butadiene copolymer graft styrene and acrylonitrile; and mixtures thereof with the copolymers described in the above item 5, for example copolymer mixtures known as ABS, MBS, ASA or AES polymers.
7. Halogenated polymers, such as polychloroprene, chlorinated rubber, chlorinated or sulfonated polyethylene, copolymers of ethylene and vinyl chloride, epichlorohydrin homo-and copolymers, preferably polymers of halogenated vinyl compounds, such as polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride; and copolymers thereof, such as vinyl chloride/vinylidene chloride copolymer, vinyl chloride/vinyl acetate or vinylidene chloride/vinyl acetate copolymer.
8. Polymers derived from alpha, beta-unsaturated acids and derivatives thereof, such as polyacrylates and polymethacrylates, polyacrylamides and polyacrylonitriles.
9. Copolymers of the monomers described in the above 8 or copolymers of the monomers described in the above 8 with other unsaturated monomers, for example acrylonitrile/butadiene copolymers, acrylonitrile/alkyl acrylate copolymers, acrylonitrile/alkoxyalkyl acrylate or acrylonitrile/vinyl halide copolymers or acrylonitrile/alkyl methacrylate/butadiene terpolymers.
10. Polymers derived from unsaturated alcohols and amines or acyl derivatives or acetals thereof, for example polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polystyrene formate, polyvinyl maleate, polyvinyl butyrate, polyallylphthalate or polyallylmelamine; and the olefin and the copolymer thereof described in the above item 1.
11. Homopolymers and copolymers of cyclic ethers. Such as polyalkylene glycols, polyethylene oxide, polypropylene oxide or diglycidyl ethers, and copolymers thereof.
12. Polyacetal. Such as polyoxymethylene and those polyoxymethylene which contain ethylene oxide as a comonomer; thermoplastic polyurethane, acrylate or MBS modified polyacetal is used.
13. Polyphenylene oxides, polyphenylene sulfides and polystyrenes; and mixtures of at least one of these with polyamides.
14. Polyurethanes derived from polyethers, polyesters or polybutadienes having terminal hydroxyl groups on one side and aliphatic or aromatic polyisocyanates on the other side, and precursors thereof.
15. Polyamides or copolyamides derived from diamines with dicarboxylic and/or aminocarboxylic acids or the corresponding lactams, for example polyamide 4, polyamide 6/6, 6/10, 6/9, 6/12 and 4/6, polyamide 11, polyamide 12, aromatic polyamides obtained by condensing metaxylene diamine with adipic acid; polyamides made from hexamethylenediamine with isophthalic and/or terephthalic acid, with or without an elastomer as modifier, such as poly-2, 4-trimethylhexamethylene terephthalamide or poly-m-phenylene isophthalamide; block copolymers of the above polyamides with polyolefins, olefin copolymers, ionomers or chemically bonded or grafted elastomers; or a block copolymer of the above polyamide with a polyether such as polyethylene glycol, polypropylene glycol or polytetramethylene glycol; and, further using EPDM or ABS modified polyamides or copolyamides.
16. Polyureas, polyimides, polyamide-imides, and polybenzimidazoles.
17. Polyesters derived from dicarboxylic acids with diols and/or hydroxycarboxylic acids or the corresponding lactones, for example polyethylene terephthalate, polybutylene terephthalate, poly-1, 4-cyclohexanedimethanol terephthalate, polyhydroxybenzoates and block copolyether esters derived from hydroxyl-terminated polyethers; and, further, polycarbonates or MBS-modified polyesters are used.
18. Polycarbonates and polyester carbonates.
19. Polysulfones, polyethersulfones and polyetherketones.
20. Unsaturated polyesters derived from copolyesters using saturated and unsaturated dicarboxylic acids with polyols and vinyl compounds as crosslinking agents, and also their halogen-containing modifications of lower flammability.
21. Crosslinkable acrylic resins derived from substituted acrylates, for example epoxy acrylates, urethane acrylates or polyester acrylates.
22. Mixtures (poly mixtures) of the abovementioned polymers, for example PP/EPDM, polyamide 6/EPDM or ABS, PVC/EVA, PVS/ABS, PVC/MBS, PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylates, POM/thermoplastic PUR, PC/thermoplastic PUR, POM/acrylates, POM/MBS, PPE/HIPS, PPE/PA6.6 and copolymers, PA/HDPE, PA/PP, PA/PPE.
23. The hydrogenated modification of a polymer according to any one of the above items 1 to 22.
Among the various polymers listed above, the resin contained in the resin composition of the present invention is preferably a thermoplastic polymer. Wherein the thermoplastic polymer preferably comprises: at least one of a vinyl aromatic polymer or hydrogenated modification thereof, a copolymer of styrene or other vinyl aromatic and diene, and a block copolymer of styrene. Here, the term "thermoplastic polymer" in the present specification means a polymer which exhibits fluidity to such an extent that it can be molded by heating, can detect at least one of a glass transition temperature and a melting point, and is softened by heating to a temperature equal to or higher than the glass transition temperature and the melting point.
The polymer may be polymerized by any known polymerization method suitable for a monomer used for forming a polymer, without any particular limitation. Further, as the polymer, a commercially available polymer can be used, of course.
Weight average molecular weight of Polymer
The weight average molecular weight of the polymer is preferably 10000 or more, more preferably 50000 or more, and preferably 1000000 or less. If the weight average molecular weight of the polymer is 10000 or more, the heat resistance and mechanical strength of the molded article formed of the resin composition can be improved. On the other hand, if the weight average molecular weight of the polymer is 1000000 or less, the moldability of the resin composition can be improved.
The weight average molecular weight of the polymer can be measured by the method described in examples.
< solvent >
The solvent that can be optionally contained in the resin composition of the present invention is not particularly limited, and examples thereof include saturated hydrocarbon solvents such as cyclohexane and aromatic hydrocarbon solvents such as toluene. In addition, when the resin composition is in the form of a solution, the content of the solvent in the resin composition can be appropriately set. In the case where the resin composition is a solid substance such as resin particles, the content of the solvent in the resin composition is 0, that is, the solvent may be substantially not contained in the resin composition.
< additive >
Other additives such as a thermal degradation inhibitor, various antioxidants, an ultraviolet absorber, a light stabilizer such as a Hindered Amine Light Stabilizer (HALS), a lubricant, a nucleating agent, an antistatic agent, an inorganic filler, a pigment, and the like may be blended to the resin composition of the present invention as required.
Some of these additives are specifically described below.
Examples of the thermal degradation inhibitor include 2-tert-butyl-4-methyl-6- (2-hydroxy-3-tert-butyl-5-methylbenzyl) phenyl acrylate (Sumilizer GM) and 1 '-hydroxy [2,2' -ethylenebis [4, 6-bis (1, 1-dimethylpropyl) benzene ] ] -1-acrylate (Sumilizer GS).
The antioxidant is not particularly limited, and examples thereof include phenol antioxidants, phosphorus antioxidants, sulfur antioxidants, and the like.
Examples of the phenolic antioxidants include Butylhydroxytoluene (BHT), 2' -methylenebis (6-t-butyl-p-cresol) (Sumizer MDP-S), 4' -thiobis (6-t-butyl-m-cresol) (Sumizer WX-R), 4' -butylidenebis (6-t-butyl-3-methylphenol) (Sumizer BBM-S), 2' -methylenebis- (4-ethyl-6-t-butylphenol) (Yoshinox 425), stearyl 3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate (Irganox 1076), pentaerythritol tetrakis [3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ] (Irganox 1010), 1, 6-hexanediol bis [3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ] (Irganox 259), 2' -thiodiethylbis [3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ] (Irganox 1035), N ' -hexamethylenebis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propanamide ] (Irganox 1098), bis [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionic acid ] [ ethylenebis (ethyleneoxide) ] ester (Irganox 245), 2,4, 6-tris (3 ',5' -Ditert-butyl-4 ' -hydroxybenzyl) mesitylene (Irganox 1330), 1,3, 5-tris [ [3, 5-bis (1, 1-dimethylethyl) -4-hydroxyphenyl ] methyl ] -1,3, 5-triazine-2, 4,6 (1H, 3H, 5H) -trione (Irganox 3114), 4- [ [4, 6-bis (octylthio) -1,3, 5-triazin-2-yl ] amino ] -2, 6-di-tert-butylphenol (Irganox 565), 2, 4-bis (octylthiomethyl) -6-methylphenol (Irganox 1520) 2, 4-bis [ (dodecylthio) methyl ] -6-methylphenol (Irganox 1726), 1,3, 5-tris [ [4- (1, 1-dimethylethyl) -3-hydroxy-2, 6-dimethylphenyl ] methyl ] -1,3, 5-triazine-2, 4,6 (1 h,3h,5 h) -trione (Cyanox 1790), 2' -dimethyl-2, 2' - (2, 4,8, 10-tetraoxaspiro [5.5] undecane-3, 9-diyl) dipropan-1, 1' -diyl = bis [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate ] (Sumilizer GA-80), 4', 4' - (1-methylpropyl-3-subunit) tris (6-t-butylm-cresol) (Adekastab AO-30), and the like.
Examples of the phosphorus antioxidant include tris (2, 4-di-t-butylphenyl) phosphite (Irgafos 168), and 4,4',4", 4' - [ [ (1, 1' -biphenyl-4, 4' -diyl) ] bis (phosphinotrigyl) ] tetraoxy ] tetrakis (1, 3-di-tert-butylbenzene) (Sandostab P-EPQ), 3, 9-bis (2, 4-di-tert-butylphenoxy) -2,4,8, 10-tetraoxa-3, 9-diphosphaspiro [5.5] undecane (Ultranox 626), 3, 9-bis (2, 6-di-tert-butyl-4-methylphenoxy) -2,4,8, 10-tetraoxa-3, 9-diphosphaspiro [5.5] undecane (Adekatab PEP-36), 2' -methylenebis (4, 6-di-tert-butylphenyl) -2-ethylhexyl phosphite (Adekastab HP-10), 2-tert-butyl-6-methyl-4- {3- [ (2, 4,8, 10-tetra-tert-butyldibenzo [ d, f ] [1,3,2] dioxa-heptyloxy) propyl } phenol, etc. (Suekatab PEP-36).
Examples of the thio antioxidant include dilauryl 3,3 '-thiodipropionate (Sumizer TPL-R), ditetradecyl 3,3' -thiodipropionate (Sumizer TPM), distearyl 3, 3-thiodipropionate (Sumizer TPS), and 2, 2-bis [ [3- (dodecylthio) -1-oxopropoxy ] methyl ] -1, 3-propane diester (Sumizer TP-D).
Examples of the metal deactivator include N, N' -bis {3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionyl } hydrazine (Irganox MD 1024), [2, 2-oxamido bis [ ethyl-3- (3, 5-di-t-butylhydroxyphenyl) propionate ] (Naugard LX-1), and the like.
Examples of the ultraviolet absorber include benzotriazole-based methylphenol (Tinuvin P), butea triazole (Tinuvin 326), 4, 6-bis (1, 1-dimethylpropyl) -2- (2H-benzotriazol-2-yl) phenol (Tinuvin 328), octaphtalotriazole (Tinuvin 329), 2- [ 2-hydroxy-3, 5-bis (. Alpha.,. Alpha. -dimethylbenzyl) phenyl ] -2H-benzotriazole (Tinuvin 234), bis-octaphtalotriazole (Tinuvin 360), 3, 5-di-tert-butyl-4-hydroxybenzoic acid-2, 4-di-tert-butylphenyl ester (Tinuvin 120), oltafenone (Chimassorb 81), oltafenone (Tinuvin 1577), 2- [4, 6-bis (2, 4-xylyl) -1,3, 5-triazin-2-yl ] -5-octaoxyphenol (Cyasorb UV-1164), 2- (4, 6-diphenyl-1, 3, 5-triazin-2-yl ] -5-octaphtaloxy-phenol (Tinuvin-5), 2- (4, 6-diphenyl-1, 3-triazin-2-yl) -5-hydroxy-1, 5-hydroxy-5-methylbenzoyl-1, 5-hydroxy-1- (Tinuvin-5-hydroxy-1-hydroxy-5-methylbenzoyl) and (Tinux-6-5-hydroxy-1-hydroxy-5-hydroxy-1 (Tinu).
As a result of the HALS, examples thereof include bis (2, 6-tetramethyl-4-piperidinyl) sebacate (Tinuvin 770), bis [1,2, 6-pentamethyl-4-piperidinyl ] 2-butylmalonate (Tinuvin 144), 2- [ [3, 5-bis (1, 1-dimethylethyl) -4-hydroxyphenyl ] methyl ] -2-butylmalonate bis [2, 6-tetramethyl-1- (octyloxy) piperidin-4-yl ] sebacate (Tinuvin 123), 1,5,8, 12-tetrakis [4, 6-bis (N-butyl-N-1, 2, 6-pentamethyl-4-piperidylamino) -1,3, 5-triazin-2-yl ] -1,5,8, 12-tetraazadodecane (Tinuvin 119) bis [2, 6-tetramethyl-1- (octyloxy) piperidin-4-yl ] sebacate (Tinuvin 123) 1,5,8, 12-tetrakis [4, 6-bis (N-butyl-N-1, 2, 6-pentamethyl-4-piperidylamino) -1,3, 5-triazin-2-yl ] -1,5,8, 12-tetraazadodecane (Tinuvin 119), reaction of N ' -bis (2, 6-tetramethyl-4-piperidinyl) polymer with 2,4, 6-trichloro-1, 3, 5-triazine and N-butyl-1-butylamine with N-butyl-2, 6-tetramethyl-4-piperidylamine (Chimassorb 2020) poly [ (6-morpholino-S-triazine-2, 4-diyl) [2, 6-tetramethyl-4-piperidinyl ] imino ] -hexamethylene [ (2, 6-tetramethyl-4-piperidinyl) imino ] (Cyasorb UV-3346), a mixture of 1, 6-hexamethylenediamine and N, reactant of N ' -bis (2, 6-tetramethyl-4-piperidinyl) with morpholine-2, 4, 6-trichloro-1, 3, 5-triazine (Cyasorb UV-3529), tetrakis (1, 2, 6-pentamethyl-4-piperidinyl) butane-1, 2,3, 4-tetracarboxylic acid ester (Adekatab LA-52) tetra (2, 6-pentamethyl-4-piperidinyl) butane-1, 2,3, 4-tetracarboxylic acid ester (Adekastab LA-57), tetramethyl 1,2,3, 4-butanetetracarboxylate and 1,2, 6-pentamethyl-4-piperidinol and beta, reactants of beta, beta ' -tetramethyl-2, 4,8, 10-tetraoxaspiro [5.5] undecane-3, 9-diethanol (Adekastab LA-63P), tetramethyl 1,2,3, 4-butanetetracarboxylate and 2, 6-pentamethyl-4-piperidinol and beta, beta, beta' -tetramethyl-2, 4,8, 10-tetraoxaspiro [5.5] undecane-3, 9-diethanol (Adekastab LA-68), and the like.
(method for producing resin composition)
The method for producing a resin composition of the present invention is characterized by comprising a heating step of heating a mixture comprising the resin and the phenol compound at 200 ℃ or higher under reduced pressure.
More specifically, the heating step may be the following steps: removing from the mixture at least a part of the solvent which can be optionally blended in the mixture and the impurities which are inevitably contained in the mixture, and drying and concentrating the mixture to obtain a resin composition in the form of a solution or a solid.
The heating temperature in the heating step is desirably 200 ℃ or higher and 400 ℃ or lower. The pressure in the heating step is preferably 50kPa or less, more preferably 20kPa or less, in terms of absolute pressure. In other words, in the heating step, the heating of the mixture to 200℃or higher is preferably performed under a pressure of 50kPa or less.
In the heating step, as long as the above temperature conditions and pressure conditions are satisfied, a direct heating drying method using a known apparatus such as a centrifugal thin film continuous evaporator, a scraped surface heat exchange type continuous reactor evaporator, or a high viscosity reactor apparatus can be carried out without particular limitation.
In addition, the step of mixing the resin and the phenol compound to obtain a mixture may be performed before the heating step. The mixing method is not particularly limited, and a method of adding a predetermined phenol compound to a solution obtained by dissolving a resin and mixing the mixture by a known method is exemplified.
Further, after the heating step, a granulating step of granulating a melt containing the resin and the predetermined phenol compound to form a granular resin composition may be performed.
(molded article)
The molded article of the present invention is obtained by molding the above resin composition. Since the molded article of the present invention contains the resin and the specific phenol compound, decomposition of the resin (polymer) is difficult to proceed even under exposure to reduced pressure and high temperature conditions, and mechanical strength and the like can be maintained satisfactorily. Moreover, the molded article of the present invention can be advantageously used as, for example, an optical lens or the like.
The molded article of the present invention can be molded into films or molded articles of various shapes according to a desired shape by a suitable known molding method. The molding method is not particularly limited, and examples thereof include injection molding, extrusion molding, blow molding, and the like. Further, as the molding method, a method of melt-spinning into nonwoven fabric or fiber by a spunbonding method, a melt-blowing method, or the like can be mentioned. The molding conditions can be appropriately set according to the materials used in molding, the desired shape of the molded article, and the like.
Examples
The present invention will be described in further detail with reference to examples, but the present invention is not limited to these examples.
The measurement and evaluation in each example were performed by the following methods. The various phenol compounds satisfying the general formula (I) were produced by the procedure described in production examples 1 to 2.
In the following description, unless otherwise specified, "%" and "parts" indicating amounts are based on mass. The pressures described in the following descriptions are absolute pressures.
The measurement and evaluation of various physical properties were performed according to the following methods.
(1) Evaluation of volatility of test sample and melting Point of phenol Compound
As test samples, phenol compounds produced in accordance with production examples 1 and 2 and various additives used in comparative examples 2 to 4 were used, respectively. 10mg of the test samples were placed in an aluminum pan, and heated from 30℃to 300℃at a heating rate of 15℃per minute using a differential thermogravimetry simultaneous measuring apparatus (manufactured by TG/DTA, hitachi High-Tech Science Corporation, product name "STA 7200") to obtain a weight loss rate after the completion of heating, and the volatility of each test sample was evaluated according to the following criteria.
A: less than 5%
B: more than 5 percent
The melting point of the phenol compound was measured using a melting point measuring instrument (product name "MP70" manufactured by Mettler-Toledo Co., ltd.) at a temperature of 20℃at a temperature of 200℃at a temperature-raising rate of 5℃per minute. The melting point of the phenol compound produced in production examples 1 and 2 was obtained in this manner.
(2) Weight average molecular weight (Mw)
The weight average molecular weight (Mw) was determined as a standard polystyrene equivalent obtained by Gel Permeation Chromatography (GPC) using tetrahydrofuran as an eluent. As the standard polystyrene, standard polystyrene manufactured by Tosoh corporation (mw=589, 1010, 3120, 9490, 13700, 37200, 98900, 189000, 397000) was used. As a measurement device, HLC8020GPC was used, and 3 columns (TSKgel G5000HXL, TSKgel G4000HXL and TSKgel G2000 HXL) were used, which were connected in series, and were carried out at a flow rate of 1.0 mL/min, a sample injection amount of 100. Mu.L and a column temperature of 40 ℃.
(3) Evaluation of ability to inhibit decomposition
The weight average molecular weight of the polymer at the time point before the heating step was defined as Mw0, the weight average molecular weight of the polymer at the time point after the granulation was defined as Mw1, and the weight average molecular weight maintenance ratio (%) =mw 1/Mw0×100 was obtained, and the ability of the test samples (phenol compounds produced according to production examples 1 and 2 and various additives used in comparative examples 2 to 4) to inhibit polymer decomposition was evaluated according to the following criteria.
A:90% or more of
B:80% or more and less than 90%
C: less than 80%
(4) Evaluation of transparency
The molded articles (flat sheets) obtained by molding the resin compositions obtained in the examples and comparative examples were subjected to a haze meter (product name NDH2000 manufactured by japan electric color industry Co., ltd.) in accordance with JIS K7136: the haze (ratio of diffuse transmittance to total transmittance:%) was measured at 2000, and the transparency of the molded article was evaluated according to the following criteria.
A: less than 0.5%
B: greater than 0.5 and less than 1.0%
C:1.0% or more
Production example 1
Into a four-necked flask equipped with a thermometer and a stirrer, 100 parts of 2, 4-bis (. Alpha.,. Alpha. -dimethylbenzyl) phenol, 133 parts of xylene, 1.2 parts of dodecylsulfonic acid, 25 parts of 10% p-tolylsulfonic acid and 4.3 parts of formaldehyde were charged, and after nitrogen substitution, the mixture was stirred at 110℃for 4 hours to obtain a reaction solution. After completion of the reaction, 2400 parts of xylene was added to the reaction mixture, and the aqueous layer was separated and removed. Thereafter, the organic layer was washed with water to neutrality. Next, the solvent was refluxed at 90 to 110℃under reduced pressure of about 200mmHg, and water was distilled off from the system. After the resulting condensation reaction mixture was cooled, 15.2 parts of triethylamine was added thereto and replaced with nitrogen, 6.8 parts of acryloyl chloride was added dropwise thereto, and the mixture was kept at 40℃for 1 hour. Thereafter, the organic layer was washed with water to neutrality, and xylene was removed by distillation under reduced pressure. Next, methanol was added to the distillation residue to precipitate crystals, thereby obtaining 87 parts of 2, 4-bis (α, α -dimethylbenzyl) -6- [ 2-hydroxy-3, 5-bis (α, α -dimethylbenzyl) ] benzyl phenyl acrylate (bisphenol monoacrylate compound, hereinafter also referred to as "phenol compound 1", represented by the following formula). When the volatility of the phenol compound 1 was evaluated as described above, the weight reduction ratio (measured value of TG/DTA) was 2.8%. Further, the melting point of the phenol compound 1 was 52 ℃.
[ chemical formula 4]
Production example 2
2, 4-bis (. Alpha.,. Alpha. -dimethylbenzyl) -6- [ 2-hydroxy-3, 5-bis (. Alpha.,. Alpha. -dimethylbenzyl) ] benzyl phenyl methacrylate (bisphenol monomethacrylate compound, hereinafter also referred to as "phenol compound 2", represented by the following formula) was obtained in the same manner as in production example 1 except that the acryloyl chloride was changed to methacryloyl chloride. The weight loss (TG/DTA measurement) obtained as described above was 2.8%. Further, the melting point of the phenol compound 2 was 57 ℃.
[ chemical formula 5]
Example 1
< thermoplastic resin preparation Process (polymerization-hydrogenation) >)
231 parts of anhydrous cyclohexane, 100 parts of dehydrated styrene, and 0.39 part of dibutyl ether were added to a reactor which was equipped with a stirring device and in which nitrogen substitution was sufficiently performed. While stirring the entire content at 60 ℃, 0.53 part of n-butyllithium (15% cyclohexane solution) was added to initiate polymerization. The whole content was stirred for 60 minutes at 60 ℃. Next, 0.18 parts of isopropyl alcohol was added to terminate the reaction, thereby obtaining a polystyrene solution.
The polystyrene solution was transferred to a pressure-resistant reactor equipped with a stirring device, and 10 parts of a diatomaceous earth-supported nickel catalyst (product name "E22U", nickel-supported amount 60%) was added as a hydrogenation catalyst, and stirred for 0.1 hour. The inside of the reactor was replaced with hydrogen, and hydrogen was supplied while stirring the solution, and hydrogenation was carried out at 180℃and a pressure of 4.6MPa for 7 hours. Thus, a reaction solution containing hydrogenated polystyrene as a polymer blended with the resin composition was obtained. The weight average molecular weight (Mw 0) of the hydrogenated polystyrene obtained was 90000.
To the reaction solution, 0.5 part of the phenol compound 1 (bisphenol monoacrylate compound) obtained in production example 1 was added and dissolved. The solution was filtered under pressure of 0.35Mpa (Dan Chuandao b mill heavy engineering company "candabac Filter") using diatomaceous earth (product name "RADIOLITE (registered trademark) # 500") as a Filter bed, and the hydrogenation catalyst was removed to obtain a colorless and transparent hydrogenated polystyrene solution.
< heating Process (concentrating Process) >)
The hydrogenated polystyrene solution was heated to 200℃under a nitrogen atmosphere, and was continuously supplied to a thin film evaporator (manufactured by Hitachi Co., ltd., product name: contro) at a pressure of 3 MPa. The operating conditions of the thin film evaporator were 13.4kPa pressure and the temperature of the internal concentrated polymer solution was 200 ℃. The concentrated solution was then continuously withdrawn from the thin film evaporator and supplied to the same type of thin film evaporator at a pressure of 1.6 MPa. The operating conditions were a pressure of 0.5kPa and a temperature of 260 ℃.
< granulating Process >
The composition containing the polymer in a molten state was continuously discharged from the thin film evaporator, extruded from a die at 200℃in a 100-stage clean room, cooled with water, and then cut with a granulator (product name "OSP-2", manufactured by Kagaku Co., ltd.) to obtain particles as a resin composition containing the phenol compound 1 (bisphenol monoacrylate compound) and hydrogenated polystyrene as a polymer. The particles were redissolved in cyclohexane and Mw1 was measured, resulting in Mw1 of 86000.
< Forming Process >
Pellets were kneaded for 1 minute at 260℃and 100rpm using a small mixer (manufactured by Micro15compound, DSM X PLore Co.) and melted, and then molded into flat plates having a length of 70mm, a width of 30mm and a thickness of 3mm using a small injection molding machine (Micro Injection Moulding Machine cc, manufactured by DSM X PLore Co.) at a molding temperature of 260℃and an injection pressure of 0.7MPa for 10 seconds and a mold holding time of 100℃using a mold temperature. The haze of the flat plate as the obtained molded article was 0.3%. Based on the obtained various measured values, various evaluations were performed as described above. The results are shown in Table 1.
Example 2
The same operations as in example 1 were carried out except that 0.5 part of phenol compound 2 (bisphenol monomethacrylate compound) was added to a reaction solution containing hydrogenated polystyrene as a thermoplastic resin, to obtain pellets and a flat plate. The Mw1 of the particles was 85500. Further, the haze of the panel was 0.4%. Based on the obtained various measured values, various evaluations were performed as described above. The results are shown in Table 1.
Comparative example 1
The same operations as in example 1 were carried out except that phenol compound 1 was not added after the hydrogenation reaction, and pellets and a plate as a molded body were obtained. The Mw1 of the particles was 60000. Further, the haze of the panel was 1.1%. Based on the obtained various measured values, various evaluations were performed as described above. The results are shown in Table 1.
Comparative example 2
Pellets and a flat plate as a molded article were obtained by performing the same operations as in example 1 except that 0.5 part of Sumilizer GS (manufactured by Sumitomo chemical Co., ltd.: acrylic acid-1 '-hydroxy [2,2' -ethylenebis [4, 6-bis (1, 1-dimethylpropyl) benzene ] ] -1-ester, the following formula) was added to a reaction solution containing hydrogenated polystyrene as a thermoplastic resin as an additive which did not satisfy the structure represented by the general formula (I). The weight reduction of the Sumilizer was 12.7%. Further, the Mw1 of the particles was 77000. Further, the haze of the flat sheet was 0.4%. Based on the obtained various measured values, various evaluations were performed as described above. The results are shown in Table 1.
[ chemical formula 6]
Comparative example 3
Pellets and a flat plate as a molded body were obtained by performing the same operations as in example 1 except that 0.5 part of Sumilizer GM (manufactured by Sumitomo chemical Co., ltd.: 2-tert-butyl-4-methyl-6- (2-hydroxy-3-tert-butyl-5-methylbenzyl) phenyl acrylate, which is an additive that does not satisfy the structure represented by the general formula (I), was added to a reaction solution containing hydrogenated polystyrene as a thermoplastic resin. The weight reduction of the Sumilizer GM was 29.5%. Further, the Mw1 of the particles was 75000. Further, the haze of the flat sheet was 0.9%. Based on the obtained various measured values, various evaluations were performed as described above. The results are shown in Table 1.
[ chemical formula 7]
Comparative example 4
The same operations as in example 1 were carried out except that 0.5 part of Irganox1010 (manufactured by BASF Japan company: pentaerythritol tetrakis [3- (3, 5-di-t-butyl-4-hydroxyphenyl) propionate ]) as an additive which does not satisfy the structure represented by the general formula (I) was added to a reaction solution containing hydrogenated polystyrene as a thermoplastic resin, and pellets and a plate as a molded body were obtained. The Mw1 of the particles was 64000. Further, the haze of the panel was 0.4%. Based on the obtained various measured values, various evaluations were performed as described above. The results are shown in Table 1.
TABLE 1
As is clear from examples 1 to 2 of table 1, bisphenol monoacrylate compounds and bisphenol monomethacrylate compounds having a predetermined structure satisfying the general formula (I) do not volatilize easily even when exposed to high temperature conditions and have sufficiently high ability to inhibit resin decomposition under reduced pressure and high temperature conditions.
On the other hand, it was confirmed from comparative example 1 that the thermoplastic resin used in example 1 was decomposed when exposed to vacuum and high temperature conditions without compounding the predetermined bisphenol monoacrylate compound or bisphenol monomethacrylate compound.
Further, as is clear from comparative examples 2 to 3, the additives which do not satisfy the general formula (I) have insufficient ability to inhibit resin decomposition under reduced pressure and high temperature conditions, and tend to volatilize easily when exposed to high temperature conditions, although they have a similar structure to the bisphenol monoacrylate compound used in example 1.
Further, as is clear from comparative example 4, the antioxidant (Irganox 1010) which is significantly different in structure from the bisphenol monoacrylate compound used in example 1 is not sufficiently capable of inhibiting resin decomposition under reduced pressure and high temperature conditions, although it is difficult to volatilize under high temperature conditions.
In examples 1 and 2, the transparency was evaluated as "a". From this, it is found that the bisphenol monoacrylate compound and the bisphenol monomethacrylate compound having a structure satisfying the predetermined formula (I) can satisfactorily suppress the coloration of the resin even when exposed to high temperature conditions.
Industrial applicability
According to the present invention, it is possible to provide a phenol compound which does not volatilize easily even when exposed to high temperature conditions and which is sufficiently high in the ability to inhibit resin decomposition under reduced pressure and high temperature conditions.
Further, according to the present invention, a resin composition containing the above phenol compound and a method for efficiently producing the above resin composition can be provided.
Further, according to the present invention, a molded article obtained by molding the resin composition can be provided.
Claims (7)
1. A phenol compound represented by the following general formula (I),
in the general formula (I), R1、R2Each independently represents a hydrogen atom or an alkyl group.
2. The phenolic compound of claim 1, wherein R of formula (I)1And R is2Each hydrogen atom.
3. The phenolic compound of claim 1, wherein R of formula (I)1Is methyl and R2Is a hydrogen atom.
4. A resin composition comprising a resin and the phenol compound according to any one of claims 1 to 3.
5. The resin composition according to claim 4, wherein the resin is a thermoplastic polymer.
6. A molded article obtained by molding the resin composition according to claim 4 or 5.
7. A process for producing the resin composition according to claim 4 or 5, comprising a heating step of heating a mixture comprising the resin and the phenol compound at 200℃or higher under reduced pressure.
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| PCT/JP2020/027523 WO2021020133A1 (en) | 2019-07-31 | 2020-07-15 | Phenolic compound, resin composition and method for producing same, and molded body |
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| EP (1) | EP4006092B1 (en) |
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| US5281646A (en) * | 1991-09-24 | 1994-01-25 | Sumitomo Chemical Company, Limited And Sumitomo Dow Limited | Production of thermoplastic resin having high impact resistance |
| US6060545A (en) * | 1997-09-29 | 2000-05-09 | Ciba Specialty Chemicals Corporation | Stabilizer mixture for organic materials |
| CN1498244A (en) * | 2001-03-20 | 2004-05-19 | �������⻯ѧƷ�ع�����˾ | Flame retardant compositions |
| JP2015122186A (en) * | 2013-12-24 | 2015-07-02 | コニカミノルタ株式会社 | Transparent electrode and electronic device |
| CN106795431A (en) * | 2014-08-27 | 2017-05-31 | 株式会社Adeka | Heat stabilizer composition and use its compound resin composition |
| CN107735451A (en) * | 2015-07-09 | 2018-02-23 | 日本瑞翁株式会社 | Resin combination, resin-formed body and optical component |
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| JPH0764786B2 (en) | 1987-12-23 | 1995-07-12 | 住友化学工業株式会社 | Phenolic compounds and stabilizers for butadiene polymers containing the same as active ingredients |
| EP0421932A1 (en) | 1989-10-06 | 1991-04-10 | Ciba-Geigy Ag | Stabilized organic material |
| KR102026593B1 (en) * | 2012-11-28 | 2019-09-30 | 디아이씨 가부시끼가이샤 | Compound containing phenolic hydroxy group, composition containing phenolic hydroxy group, resin containing (meth)acryloyl group, curable composition and cured product thereof, and resist material |
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- 2020-07-15 CN CN202080036904.3A patent/CN113840872B/en active Active
- 2020-07-15 WO PCT/JP2020/027523 patent/WO2021020133A1/en unknown
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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5281646A (en) * | 1991-09-24 | 1994-01-25 | Sumitomo Chemical Company, Limited And Sumitomo Dow Limited | Production of thermoplastic resin having high impact resistance |
| US6060545A (en) * | 1997-09-29 | 2000-05-09 | Ciba Specialty Chemicals Corporation | Stabilizer mixture for organic materials |
| CN1498244A (en) * | 2001-03-20 | 2004-05-19 | �������⻯ѧƷ�ع�����˾ | Flame retardant compositions |
| JP2015122186A (en) * | 2013-12-24 | 2015-07-02 | コニカミノルタ株式会社 | Transparent electrode and electronic device |
| CN106795431A (en) * | 2014-08-27 | 2017-05-31 | 株式会社Adeka | Heat stabilizer composition and use its compound resin composition |
| CN107735451A (en) * | 2015-07-09 | 2018-02-23 | 日本瑞翁株式会社 | Resin combination, resin-formed body and optical component |
Also Published As
| Publication number | Publication date |
|---|---|
| EP4006092B1 (en) | 2024-05-01 |
| JPWO2021020133A1 (en) | 2021-02-04 |
| EP4006092A1 (en) | 2022-06-01 |
| TWI828931B (en) | 2024-01-11 |
| KR20220041826A (en) | 2022-04-01 |
| CN113840872A (en) | 2021-12-24 |
| TW202110784A (en) | 2021-03-16 |
| EP4006092A4 (en) | 2023-08-23 |
| US20220234986A1 (en) | 2022-07-28 |
| WO2021020133A1 (en) | 2021-02-04 |
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